$216 Find Cheap Flights from Hawaii to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 10/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Flight Deals

Cheap Flights from Hawaii to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hawaii to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hawaii to Chicago

Fri, Sep 18 - Mon, Sep 28
Multiple Airlines Logo
6:00 am - 11:57 pm
KOA
-
ORD
12h 57m
2 stops
Multiple Airlines Logo
6:01 am - 2:51 pm
ORD
-
KOA
13h 50m
1 stop
$492Multiple Airlines
Wed, Sep 9 - Wed, Sep 16
Alaska Airlines Logo
10:35 am - 1:22 pm
KOA
-
ORD
21h 47m
1 stop
Alaska Airlines Logo
6:01 am - 2:51 pm
ORD
-
KOA
13h 50m
1 stop
$494Alaska Airlines
Wed, May 27 - Sat, May 30
Delta Logo
9:55 pm - 4:49 pm
LIH
-
ORD
13h 54m
1 stop
Delta Logo
12:47 pm - 7:06 pm
ORD
-
LIH
11h 19m
1 stop
$494Delta
Fri, Sep 18 - Tue, Sep 22
Multiple Airlines Logo
6:00 am - 11:57 pm
KOA
-
ORD
12h 57m
2 stops
Multiple Airlines Logo
7:59 pm - 2:51 pm
ORD
-
KOA
23h 52m
1 stop
$499Multiple Airlines
Wed, May 27 - Sat, May 30
Delta Logo
9:55 pm - 4:49 pm
LIH
-
ORD
13h 54m
1 stop
Delta Logo
6:24 am - 7:06 pm
ORD
-
LIH
17h 42m
2 stops
$500Delta
Wed, Sep 9 - Wed, Sep 16
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
Southwest Logo
8:50 pm - 12:25 pm
MDW
-
KOA
20h 35m
2 stops
$505Southwest
Wed, May 27 - Sat, May 30
Delta Logo
8:40 pm - 6:33 pm
LIH
-
MDW
16h 53m
2 stops
Delta Logo
9:22 am - 7:06 pm
MDW
-
LIH
14h 44m
2 stops
$505Delta
Wed, Sep 9 - Wed, Sep 16
Southwest Logo
10:00 am - 5:40 am
KOA
-
MDW
14h 40m
2 stops
Southwest Logo
8:50 pm - 12:25 pm
MDW
-
KOA
20h 35m
2 stops
$510Southwest
Fri, Aug 21 - Sun, Aug 30
American Airlines Logo
9:40 pm - 10:59 pm
LIH
-
ORD
20h 19m
1 stop
American Airlines Logo
7:15 am - 2:55 pm
ORD
-
LIH
12h 40m
1 stop
$532American Airlines
Fri, Oct 30 - Mon, Nov 2
American Airlines Logo
6:00 pm - 7:10 am
HNL
-
ORD
8h 10mnonstop
American Airlines Logo
10:00 am - 3:15 pm
ORD
-
HNL
9h 15mnonstop
$535American Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$216
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 29% increase in price.
Flight from Lihue to Chicago O'Hare Airport

FAQs for booking flights from Hawaii to Chicago

  • How does KAYAK find such low prices on flights from Hawaii to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hawaii to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hawaii to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hawaii is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Hawaii to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hawaii with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hawaii to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hawaii up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Schererville
Chesterton
Munster
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Hawaii

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.